A Gentleman’s Guide to Planning the Perfect Date

Asking out a woman you like (or could potentially like) is a very intimidating thing. But if you take the leap, congratulations — you’ve already surpassed hurdle one of dating. She said yes. She agreed to go out with you; she liked something about you, and now it’s on to exploring that connection. It’s on to the first date — that interview-like meeting over dinner where you both get to know each other and determine if there is a possibility of compatibility. Not to put too much pressure on you gentlemen, but you should be making every effort possible to plan ahead and make the date perfect. Don’t let a bad date be the reason she rejects you — at least take comfort in that aspect of it.

Gentlemen, here’s how to plan the perfect first date (and dates afterwards).

1. Observe the 4 p.m. deadline

As the big date approaches, women worry that they’ll be stood up. This is why there is an unofficial 4 p.m. deadline to confirm the date (again). If your date is scheduled for 8 p.m. then it’s the gentlemanly thing to do to call and confirm. If you call at 4:20 p.m. to confirm an 8 p.m. date, then she may figure that she’s been stood up and make other plans to protect herself from a letdown. Don’t be that guy. The 4 p.m. deadline means that it’s OK to call between noon and 4 p.m.

2. Choose the location well

If you are both living in a city, then the first date rule is as follows: The planned location of the date should be closer to her place than yours so you can walk her home. Also, you should reach your planned meeting place on time or a little earlier than her. If you’re driving to pick her up at her place, make sure to also observe proper car etiquette — get out of the car to greet her, and make sure you open the door for her. Chivalry is not dead, and it leaves a lasting impression on her that you’re a gentleman.

3. Dress the part

The way you present yourself is important. Never forget that. It’s human nature to judge someone on the way they look. A woman will do this, and rightfully so. That means don’t look like a slob, be presentable, and remember to always keep a positive attitude and smile.

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4. Pay attention to her

Women spend a lot of time getting ready, looking beautiful, and wondering if you men notice. Respond to her efforts. Women love being told they’re beautiful (especially if it’s genuine).

5. But don’t go overboard with the compliments

You should pay her a few thoughtful compliments, and they should be sincere. Let her know if you like her smile or her eyes. Now you have her attention. Don’t forget to add in a few that are unrelated to her looks, like her intelligence or the way she speaks passionately about something. This is your “in” with her.

6. Money matters

Spending too much money on a date makes a woman think that you’re trying to buy her affection. Go somewhere affordable, casual, and nice. There should be no pressure attached to the evening. Leave your expensive dates for when you’re in a relationship.

7. Introduce her

If you happen to run into someone you know or talk to absolutely anyone, make sure to introduce her within 30 seconds without using the words “my friend.” Personal details are required. To note: By date six, she should have met at least one of your close friends.

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8. Don’t woo her with material things

Unless a woman is a noticeable, hopeless social climber, you won’t impress her with what you own (if you even own anything). Instead, just be yourself, and she will discover what’s valuable about you, rather than material, superficial things.

9. Notice what she’s drinking

Pay attention to what she orders. If she’s having a glass of wine, ask her if she would like a refill when the glass is empty. It makes you seem more attentive and thoughtful. It also makes a woman feel good that you remember the details of things that make her happy.

Remember, you two: Don’t overdo it with the drinking.

10. Walk her to her door

Not only is it the gentlemanly thing to do, but it’s a scary world, and she wants to feel protected by you, knowing that you saw her safely home. If she invites you in as a polite gesture, do not have any expectation and just go with the flow.

11. Kiss her

If the date has gone well (it’s something that you will just know), a kiss should somehow come into play, even if it’s just a peck. This is reassurance to her that you like her. But don’t be discouraged if she hesitates to kiss you in return — she might be shy or nervous that she likes you. Now is your chance to ask her on a second date.